INTRODUCTION TO

Essential oils

GBPP
TEKNOLOGI MINYAK ATSIRI DAN
FITOKIMIA

Pengenalan minyak atsiri

Pemanfaatan, jenis, definisi, komponen atsiri

Penggolongan senyawa dalam

minyak atsiri

Terpenoid, benzen, rantai lurus,

senyawa N,S

Reaksi senyawa minyak atsiri

Esterifikasi, reduksi, oksidasi, hidrolisis,

adisi

Isolasi/Ekstraksi dengan metode penyulingan

Prinsip, tipe kondensor, peristiwa, jenis penyulingan,
keunggulan, kerusakan, faktor yang mempengaruhi, alat
dan proses penyulingan

Isolasi minyak atsiri dengan metode adsorbsi

Prinsip, faktor yang mempengaruhi daya adsorbsi,
rendemen dan mutu, pembuatan lemak, syarat bunga,
proses, cara adsorbsi enfleurasi dan maserasi

Isolasi minyak atsiri dengan metode solvent

extraction
prinsip, deret eutropik pelarut, syarat pelarut, skema
proses, daerah kritis penyebab loss pelarut

Isolasi minyak atsiri dengan metode press/kempa

Prinsip dasar, syarat bahan yang dikempa

Analisis sifat fisikokimia

Bilangan iod, putaran optik, kelarutan dalam etanol,
bilangan asam, bilangan ester, analisis komponen utama,
analisis GC

Volatile Oils, Essential oils,

Ethereal oils
Oily

liquids, which are entirely or almost

entirely volatile without decomposition

Plant

products, giving the odors and tastes

characteristic of the particular plant, thus
possessing the essence.

Ether

like in their volatility.

ESSENTIAL/VOLATILE OILS
All official volatile oils are
of vegetable origin.
Normally pre-exist in the
plant stored in a
special secretory tissue
(e.g. Citrus peel oil cells
or oil ducts in
umbelliferous fruits).

WORLD ESSENTIAL OIL TRADE

World total essential oil value >USD 4 billion,

average growth/yr >5%
Indonesian export >USD120 million
Worls essential oil trade >300 items
Indonesia >40 items, commercialized or
potentially

World Major Essential Oils

approx. volume for 2007
Essential Oil

Production (MT)

Major Source

Derivative Prod.

Orange

51,000

Brasil, USA

High

Cornmint

32,000

India, China

High

Lemon

9,200

Argentine, Spain

High

Eucalyptus

4,000

China, India

Medium

Peppermint

3,300

USA, India

Medium

Citronella

1,800

China, Indonesia

Medium

Clove Leaf

1,800

Indonesia,
Madagascar

High

Sassafras

1,800

China

High

Lime

1,800

Mexico,

Low

Lavandin

1,300

France, Spain

Low

Patchouli

1,200

Indonesia, China

Low

Brian Lawrence- Perfumer & Flavourist v.34 January 2009

INDONESIAN AROMATIC PLANTS

Clove
Nutmeg
Benzoin
Cinnam
on
Citronell
a
Clove
Nutmeg
Patchoul
i
Pepper

Cajepu
t Clove
Nutme
g

Massoi
a
Cajeput
Canang
a
Citronell
a
Clove
Cubeb
Galanga
Ginger
Kaffir

Sandalwoo
Indonesia is #1 grower of
d
Cajeput, Cananga, Clove, Cubeb, Galanga,
Kaffir lime, Massoia, Nutmeg, Patchouli

Clove

Indonesia is # 2-5 grower of Benzoin,

Cinnamon, Ginger, Pepper
Sandalwood, Vetiver

Indonesian Essential Oil Production 2009

Total production 5000-6000 tons, USD 125-150 mill
80% of export comes from 3 main oils
60% essential oil, 30% derivative products for export, 10%
industry (food, cosmetic, consumer goods, pharmacy)

No

Items

Output (MT)

Remarks

Clove/Stem Leaf

1,900-2,000

Patchouli

Nutmeg

350-400

Citronella

300-400

Domestic > Export

Cajeput

200-300

Mostly for domestic

Gurjun

50-60

Vetiver

25-30

Cananga

12-15

Massoia

12-13

10

Eaglewood (aetoxylon sympetalum)

10-12

11

Lajagoa (alpina malaccensis)

3-4

12

Cubeb

2-3

13

Sandalwood

1-2

14

Kaffir Lime Leaf

1-2

Mostly for derivatives

900-1,000

FUNCTION OF
VOLATILE OILS
In most cases, the biological
function of the terpenoids of
essential oils remains
obscure it is thought that
they play an ecological role
protection from predators
& attraction of pollinators.

Function
Attracting

(help polination) or repelling

insects
Protection from heat or cold
As antibacterial agents
Uses : Pharmacy, aromatherapy,
Perfumery, Food technology

LOCALIZATION
Synthesis & accumulation of essential oils are
generally associated with the presence of
specialized histological structures, often located
on or near the surface of the plant:
- Oil cells of Zingiberaceae
- Glandular trichomes of Lamiaceae
- Secretory cavities of Myrtaceae or Rutaceae
- Secretory canals of Apiaceae or Astereraceae
(Compositeae)

Localization
Usually in specialized histological structures

Distribution

In higher plants, different families as: Rutaceae,

Myrtaceae, Lamiaceae (Labiatae), Lauraceae
Accumulate in all types of vegetable organs:
Flowers (rose), Leaves (eucalyptus),
Barks (cinnamon)

Woods (Sandalwood)

Rhizomes (ginger),

Stem bark (cinnamon)

Fruits (star anise),

Roots (vitiver.)

Seeds (nutmeg).

May occur associated with other constituents: gums

(oleogums), resins (oleoresins) gums & resins (oleogumresins)

An essential oil is a concentrated hydrophobic liquid containing volatile

aroma compounds from plants.
Essential oils are also known as volatile oils, ethereal oils or aetherolea
Essential oils are derived from various sections of plants.
Berries
Allspice
Juniper
Seeds
Almond
Anise
Celery
Cumin
Nutmeg oil
Bark
Cassia
Cinnamon
Sassafras
Wood
Camphor
Cedar
Rosewood
Sandalwood
Agarwood
Rhizome
Galangal
Ginger

Leaves
Basil
Bay leaf
Cinnamon
Common sage
Eucalyptus
Lemon grass
Melaleuca
Oregano
Patchouli
Peppermint
Pine
Rosemary
Spearmint
Tea tree
Thyme
Wintergreen
Resin
Frankincense
Myrrh

Flowers
Cannabis
Chamomile
Clary sage
Clove
Scented geranium
Hops
Hyssop
Jasmine
Lavender
Manuka
Marjoram
Orange
Rose
Ylang-ylang
Peel
Bergamot
Grapefruit
Lemon
Lime
Orange
Tangerine
Root
Valerian
Vetiver

Decomposition
In some cases the essential oils dont pre-exist but
formed by decomposition of a glycoside
-Benzaldehyde (amygdalin) in bitter almond
-Allyl isothiocyanate(sinigrin) in black mustard

USES OF VOLATILE OILS

Therapeutically (Oil of Eucalyptus)

Flavouring (Oil of Lemon)
Perfumery (Oil of Rose)
Starting materials to synthesize
other compounds (Oil of Turpentine)
Anti-septic due to high phenols
(Oil of Thyme). Also as a
preservative (oils interfere with
bacterial respiration)
Anti-spasmodic (Ginger, Lemon
balm, Rosemary, Peppermint,
Chamomile, Fennel, Caraway)
Aromatherapy

DEFINITION OF VOLATILE OILS

Volatile oils are products which are generally complex in
composition, consisting of the volatile principles
contained in plants, and are more or less modified
during the preparation process.
Only 2 procedures may be used to prepare official oils
i.
Steam distillation
ii.
Expression
4 Main types of volatile oils
iii.
Concretes
iv.
Pomades
v.
Resinoids
vi.
Absolutes

CONCRETES
Prepared from raw materials of
vegetable origin (bark,
flowers, leafs, roots etc.)
Extracted by HC type solvents,
rather than distillation or
expression Becomes
necessary when the
essential oil is adversely
affected by hot water or
steam (e.g. jasmine).
Produces a more true-to-nature
fragrance.

CONCRETES
Concretes contain about
50% wax and 50%
essential oil (jasmine).
Ylang ylang (concrete
volatile) contains 80%
essential oil and 20%
wax.
Advantages of concretes:
they are more stable
and concentrated than
pure essential oils.

POMADES
True pomades are (volatile
oil) products of a process
known as enfleurage
(hot or cold).
Enfleurage is used for
obtaining aromatic
materials from flowers
containing volatile oils to
produce perfume long
after they were cut.

ENFLEURAGE: METHOD
A glass plate is covered with a thin
coating of especially prepared and
odourless fat (called a chassis).
The freshly cut flowers are individually
laid on to the fat which in time
becomes saturated with their
essential oils. The flowers are
renewed with fresh material.
Eventually the fragrance-saturated fat,
known as pomade, may be treated
with alcohol to extract the oil from
the fat.

RESINOIDS
Prepared from natural
resinous material (dried
material) by extraction
with a non-aqueous
solvent, e.g. Petroleum
ether or hexane.
E.g. Balsams Peru
balsam or benzoin;
resins (amber or mastic);
Oleoresin (copaiba
balsam and turpentine);
Oleogum resins
(frankincense and myrrh)

RESINOIDS
Can be viscous liquids,
semi-solid or solid.
Usually homogeneous
mass of noncrystalline character.
Uses: in perfumery as
fixatives to prolong
the effect of a
fragrance.

ABSOLUTES

Obtained from a concrete,

pomade, or a resinoid by
alcoholic extraction.

The extraction process may be

repeated.

The ethanol solution is cooled &

filtered to eliminate waxes.

The ethanol is then removed by

distillation.

They are usually highly

concentrated viscous liquids.

Aromatic material
of natural origin
Essential Oils
obtained by

Distillation
Oil

Aromatic extracts
obtained by

Expression

Solvent
Extraction

Enfleurage

Resinoids

Pomades

Citrus oil

Concretes
Absolutes

Enfleurage
absolutes

Physical properties
Possess characteristic odors
Liquids and volatile at ambient temp.
Soluble in common organic solvents. Sparingly
soluble in water, however sufficient to produce
aromatic water.
Specific gravity (0.8-1.17), mostly lighter than
water (clove and cinnamon are heavier).
Have high refractive index and most of them
rotate the plane of polarized light.

Comparison between fixed oils and

essential oils
Their

volatility
When smeared on paper
Oxidation (resinified, fixed oil rancid)
Chemical structure
Saponification by KOH (NOT saponify)

CHEMICAL COMPOSITION
Volatile oils are divided into 2 main classes based
on their biosynthetic origin
i.

Terpene derivatives (formed via the acetate

mevalonic acid pathway)

ii.

Aromatic compounds (formed via the shikimic

acid-phenylpropanoid route)

iii.

Miscellaneous Origin

VOLATILE OIL COMPOSITION

Mixtures of HCs and oxygenated

compounds derived from these HCs.

Oil of turpentine mainly HCs

Oil of Clove mainly oxygenated compounds

EXCEPTION: Oils derived from

glycosides (e.g. bitter almond oil & mustard oil).
Oxygenated compounds responsible
for the odour/smell of the oil. They are
slightly water soluble Rose water & Orange
Water; more alcohol soluble.

Most volatile oils are terpenoid. Some

are aromatic (benzene) derivatives mixed
with terpenes.
Some compounds are aromatic, but
terpenoid in origin (e.g. Thymol Thyme)

NUTMEG & NUTMEG OIL

Definition: Nutmeg is the
dried kernel of the seed
of Myristica fragrans
(Myristicaceae).
Geographical Sources
Indigenous to the Molucca
Islands (Spice Islands)
Cultivated in Indonesia,
Malaysia & the West
Indies.

NUTMEG OIL
Nutmeg oil is distilled from the
kernels of Myristica fragrans.
CONSTITUENTS
Pinene
Sabinene
Camphene
Dipentene
Safrole
Eugenol & eugenol derivatives
Myristicin a benzene: toxic to
humans (large does of nutmeg
or nutmeg oil may cause
convulsions).

MACE CONSTITUENTS
Consists of the dried arillus
or arillode of M. fragrans.
Description: bright red
colour & lacks in aroma
CONSTITUENTS
Volatile oils (similar to that
of nutmeg) eugenol
derivatives are the main
active constituents
responsible for the antibacterial effects.
Also has 2 anti-microbial
resorcinols (Malabaricone
B and C)

Used for carminatives,

flavouring, infantile diarrhoea
(Tea of nutmeg Ayurveda).

CLOVE
DEFINITION: Cloves are the dried
flower buds of Syzygium
aromaticum (Eugenia
caryophyllus), (Myrtaceaea).
Cloves are 10-17.5 mm long.
The head consists of 4 slightly
projecting calyx teeth, 4
membranous petals and
numerous incurved stamens
around a large style.
Odour: Spicy & Pungent
Taste: Aromatic
Oil of cloves is yellow or colourless,
is slightly heavier than water.

CLOVE OIL - CONSTITUENTS

14-21% Volatile oils
mainly eugenol, isoeugenol, &
acetyleugenol
Sesquiterpenes( and
caryophyllenes)
Stigmasterol, Campesterol, Tannins
Triterpene acids & esters, Glycosides
Oil of clove like other
volatile/essential oils should be
stored in a well-fitted, air-tight
container, & should be protected
from light & heat.

Derivatives of Clove Oil

HO

ETHYL ISOEUGENOL
O

O
O

METHYL
ISOEUGENOL

ISOEUGENYL
ACETATE

PROPENYL
GUAETHOL

HO

VANILLIN

BENZYL ISOEUGENOL

O
O

O
O

CARYOPHYLLENE
ACETATE

O
O

HO

HO

EUGENYL ACETATE METHYL EUGENOL ISO EUGENOL

BENZYL EUGENOL

DIHYDRO
EUGENOL
Distillation

CH3

O
HO

H
H3C

CH2

EUGENOL

Fractionatio
n
Acetylation

CH3

CARYOPHYLLENE
CLOVE OILS

CLOVE BUD/LEAF/STEM

Isomerisati
on
Methylation
Hydrogenat
ion
Oxidation

CINNAMON: Cinnamomum zeylanicum

Individually scraped barks are placed
inside each other
Consists of a single or double
compound quill about 6-10 mm
diameter
Thickness : good quality: Not > 0.5mm,
bark: 10-40mm.
External surface: is yellow-brown,
shining, wavy lines (pericycle fibres)
and occasional scars & holes
(leave/twig positions).
Inner surface: darker, longitudinally
striated.
Odour: fragrant
Taste: Warm, sweet & aromatic

Cinnamomum - CONSTITUENTS
Volatile

oils (at least

1.2 %)
Phlobaphenes
Mucilage
Calcium Oxalate
Starch

EUCALYPTUS
DEFINTION: Eucalyptus
leaf consists of the whole
or cut dried leaves of the
older branches of
Eucalyptus globulus,
(Myrtaceae).
GEOGRAPHICAL
SOURCES
Portugal, SA, Spain, China,
Brazil, Australia, India &
Paraguay.

CHARACTERISTICS &
CONSTITUENTS
CHARACTERISTICS
Colourless or pale yellow
liquid
Aromatic & camphoraceous
in odour.
Pungent & camphoraceous
in taste, which is followed
by a sensation of cold.
CONSTITUENTS
At least 70 volatile oils
(mainly cineole).

GINGER

Scraped/peeled herb
has little resemblance to
the fresh herb (loss in
weight & shrinkage)
Cork cells high starch
content
Outer zone of flattened
parenchyma & inner
zone of normal
parenchyma.
Oil cells scattered in the
cortex.

Zingiber officinale - CONSTITUENTS

Volatile oils (1 2%)

Gingerol pungent component

Anti-inflammatory
Shogaols increases bile
secretion
Sesquiterpene HCs

Camphene
Cineole
Citral
Borneol

Zingiberene & Zingiberol

(Sesquiterpene alcohol)

Resins
Starch
Mucilage

LEMON OILS - Oleum limonis

Definition: Dried lemon (Limonis
Cortex) peel is obtained from the
fruit of Citrus limon (Rutaceae).

Dried lemon peel occurs in

spiral bands (2 cm wide; 23 mm thick).
The outer surface is rough &
yellow; the inner surface is
pulpy & white (anatomically
similar to that of an orange
peel).
Odour: Strong &
characteristic
Taste: aromatic & bitter

LEMON OILS - Oleum limonis

Definition: Lemon oil is the oil
expressed from the outer part of
the fresh pericarp of the ripe or
nearly ripe fruit of Citrus limon
(Rutaceae).
Oil should be obtained by suitable
mechanical means, without the use
of heat, from the fresh peel.
Much oil is derived via steam
distillation, but this process yields
oil of inferior quality.
Distilled oil of lemon is much cheaper
than that prepared by expression.
Large amounts are used for nonpharmaceutical purposes.

Oleum limonis - CONSTITUENTS

Terpenes mainly
limonene
Sesquiterpenes
Aldehydes (Citral &
Citronella)
Esters
Lemon oil has a
tendency to
resinify and
should be
protected from the
action of air & light
as much as
possible.

TERPENELESS
LEMON OIL
Definition: Oil prepared by
concentrating lemon oil in
vacuum until most of the
terpenes have been
removed, or by solvent
partition. The
concentrate is a
terpeneless oil, which has
a citral content of 40-50
%.
It is equal in flavouring to
10-15 times its volume of
lemon oil

TYPICAL FORMULA OF
FRAGRANCE COMPOUND
(JASMINE)
BENZYL ACETATE
50%
1-PMETHEN-8-OL
10%
METHYL-2AMINOBENZOATE
5%
4-(2,5,6,6TETRAMETHYL-2-CYCLOHEXEN-1-YL)-3-BUTEN-2-ONE
5%
3-METHYLBUTYL O-HYDROXYBENZOATE
5%
ALPHA-CINNAMALDEHYDE
5%
CANANGA OIL
5%
PETITGRAIN OIL
5%
STYRAX
5%
MUSK XILENE
3%
RECTIFIED CLOVE LEAF OIL
2%

ESSENTIAL OIL in FRAGRANCE COMPOUND: 10 25%

FRAGRANCE COMPOUND IN SOAP: 1 1.2%,

TERIMA KASIH